


Odds

by LaughableLament



Series: Wincestmas [3]
Category: Supernatural
Genre: 12 Days of Wincestmas, And a Feather Boa, Blow Jobs, Established Relationship, Genderplay, Hand Jobs, M/M, PWP, Pre-Series, Sam in a Skirt, Standard Stanford Angst, Stanford Era
Language: English
Status: Completed
Published: 2017-01-12
Updated: 2017-01-12
Packaged: 2018-09-16 23:16:38
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 952
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/9294062
Author URL: https://archiveofourown.org/users/LaughableLament/pseuds/LaughableLament
Summary: “Thought I’d surprise you for Christmas.” Dean’s on his feet. “Looks like I’m the one gets the surprise.”





	

**Author's Note:**

  * For [thep0rnfairy (Jesibella)](https://archiveofourown.org/users/Jesibella/gifts).



Geekboy’s roommate got real helpful once Dean tossed him a Benjamin and told him to kick rocks. Said Sam was at some sorority party—which, _nice, bro!_ —and oughta be back around three.

Dean gets settled, naps what he can. Wonders how Sam rests for shit on this lumpy rack. Key click-scrapes and Dean—doesn’t strike a pose, exactly…

 _Ohhh, shit. Sammy brought a chick home_. Then: _Hope she don’t mind sharin’_ and _Fuck, she’s…_

Tall. Red-slippered feet and muscled calves. Snow-patterned stockings with lace at the top and sweet red bows, one above each knee.

“D-Dean?” Sam jerks his coat closed. Backlit against the hall but Dean can hear him blush.

“Thought I’d surprise you for Christmas.” Dean’s on his feet. “Looks like I’m the one gets the surprise.” Step or two closer and that’s no scarf around Sam’s neck. “Feathers?” Now he can see Sam pink up.

He ducks past. “Cut it out, asshole.”

Dean locks the door and jams a chair under the knob. Just in case homeboy thought he’d been kiddin’ about _stay gone_. “Show me.” Dean leans against a cluttered desk, cotton-mouthed.

Sam puffs up like to fight but Dean tips his head. Only ragging his brother cause it’s his job. Truth is Sam’s— _Jesus, he’s beautiful_. Arched brows, lined eyes, glossed lips. Almost not-made-up and it’s—

Sam drops his coat and Dean decides the one little desk lamp ain’t gonna cut it. Fluorescents pop and Sam folds his arms, red as his dress and Dean has to pinch his balls a little to settle down.

“Mrs. Claus, I take it.”

Modest cut, crushed velvet and trimmed with more of those feathers. Full skirt right above his stocking tops.

“That’s crack investigating Dean, you oughta—”

“Lose a bet or we bookin’ a trip to Thailand?” Dean runs hands up Sam’s side, nap prickles his palms. Staves shift underneath when Sam laughs.

“Odds.” Sam shivers. Dean ghosts up his neck. “It’s a drinking game, you’d like it, it ruins lives.”

“Oh I like it loads so far,” Dean tugs at a sleeve. “You gonna show me what’s underneath?

Sam turns red all over again but unwinds his boa. “Say anything and I’ll cut you, I swear to God.”

Off goes the dress and Dean takes in Sam’s shoulders, dark and wide as they’ve ever been and his hair, swept to one side and soft-curled around his ears. White, some kinda corset thing hugs his waist and flares at his hips. Sheer little cups and okay—rolled-up-sock boobs, that’s pretty hilarious but the plaid purple boxers reeaally sell it.

“I drew the line at the thong,” Sam grits.

“Aw, shit, Sammy.” Dean bites lips and Sam’s glare drops the temp about five degrees. “I’m sorry, man. I’m sorry.” He’s not. “Why don’t you lose those, huh? Hidin’ all the good stuff anyway.”

Sam’s jaw works like he’s racking a round and Dean can’t allow that. Takes matters into his own—well…

Sam gasps when his shorts hit his feet and Dean mouths over his crown. Up above all that lace Sam tips back. Hands fall heavy and they ripple together. Sam moans.

Lean hairy thighs and then stiff lace and smooth nylon and Sam’s lips, shiny-pink in his snarl. Dean hits a whole new world of wires crossed, beautiful-baby-girl-brother and gettin’ his face fucked. Concrete bleeds cold ache up his knees and Sam hip-rolls a little faster. Dean bobs from his shoulders, pulls with his cheeks. Flicks tongue all up the underside and bats his lashes at Sam. Stone grip on his cinched waist in case he goes over and—

Dean tastes the first shot, throats the second and Sam vibrates above him, leans on him and thrusts. Last second Dean pulls off, opens wide and Sam’s aftershock flares hot on his tongue, across his lips. Sam’s nails dig in his back and that face, that face right there? Everything.

Sam pulls him up, shoves him back and topples books and papers. Lip gloss tastes like peaches and mouth like wintergreen. Both try to get Dean’s belt off; then Sam’s whipping it through the loops and Dean never regretted a button fly more in his life.

Sam’s hand, hot and insistent. “You get off on this hard, huh?” Dean’s head thumps the wall. “Sucking your baby sister’s cock?”

“Oh, fuck,” he maybe says, loses a minute or two. Sam jerks him rough and perfect ’til he punch-grunts, shoots up his shirt and gets air, hips off the desk and arms around Sam’s neck. Sam tugs clothes, tangles legs and tumbles them into the bed. Kneels above Dean, straddles his thighs.

“You wanna fuck me in this, I take it.”

“Oh hell yes,” he mumbles, fucked dumb already and still wearing jeans around one ankle. “I wanna _everything_ you in that.” Sam’s hairdo sticks everywhere. Eyeliner trails to his cheek tops and mouth, bright-shiny now for a whole ’nother reason and it’s fuckin’ smokin’. “But,” Dean yawns. “I drove twenty hours to get here…”

“Dean…”

“I know, I know.”

Sam gets quiet. “How long can you stay?”

Dean shrugs. “Found a Maenad cult maybe, up in Napa. You got a few weeks off, you could—”

Sam kisses his mouth shut.

Which means no.

Dean opens up anyway, licks and coaxes; Sam does his caveman thing. Dean memorizes every move, swallows every breath until Sam winds down, brands his ribs in lazy circles.

“You won’t,” Sam whispers, “take off while I sleep?”

“Fuckin’… what? Jesus, Sammy, no!”

“Okay.” Sam gets up and loses the lingerie, which is tragic. Cuts the lights, crawls back in. “I’m glad you’re here.”

“Me too, man.” Dean trails knuckles up and down Sam’s arm. “Me too.”


End file.
